I can enter a free board from my assistent, I want to upgrade but every time I end up in a loop saying "can't find page"
If your assistant has invited you as a guest on their board, then you cannot upgrade the workspace. You have to be an admin/member of a free workspace to upgrade it. You can ask your assistant to add you as a member. Here is how to do it https://support.atlassian.com/trello/docs/inviting-people-to-a-workspace/
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